


Wincest Diaries

by purpleskiesandcherrypies



Category: Supernatural
Genre: Angst, Fluff, Happy Dean Winchester, Happy Sam Winchester, M/M, Pining, Sad Sam Winchester, Smut, Wincest - Freeform
Language: English
Status: Completed
Published: 2019-01-05
Updated: 2019-01-27
Packaged: 2019-10-04 22:42:55
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 25
Words: 4,211
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17313212
Author URL: https://archiveofourown.org/users/purpleskiesandcherrypies/pseuds/purpleskiesandcherrypies
Summary: Drabble Wincest Diaries for evey day throughout January; filled with angst, fluff and a little smut





	1. Chapter 1

Dean had to drag Sam from the car, literally. He was still in a state of shock, didn’t say a word on their way here.

“Je...” Sam mumbled, his voice cracking before he could say the last syllable.

“I know, Sammy.” Dean draped one of Sam’s arm over his shoulder, lifting up his kid brother who grew to be taller than him and a couple of pounds heavier, too. But it doesn’t matter. 

Dean will always have Sam. Dean will always carry Sam’s burden as if it was his own. 

“Jess..” 

“I know. I’m sorry, Sammy.” Dean laid Sam on the bed and took off his shoes for him. “Get some rest. Do you want to take a shower?”

“No, Dean. You don’t understand. We have no time to rest.” Sam was sitting up now, his eyes grew wide, as if he just registered where he was. As if he just realized what happened.

“We can do nothing today, Sammy. Gotta wait. We’ll get him, I promise.” Dean sat next to Sam and to his surprise, Sam laid his heavy head on Dean’s shoulder, almost drifting off to sleep in this position. He must be really tired.

“Promise? Will you help me?” Sam asked, his voice already a whisper.

“Promise, Sammy. I got you.” 


	2. #2

Three days and Sam starts to get better. Time heals wounds, they say. Apparently, they’re right. He starts to eat again but was still eager to search for the demon. And when Dean saw his brother slowly getting better again, finally he’s been able to breath, too.

“We’ll get him, Sammy.” Dean brushed the strand of hair out of Sam’s face as he laid curled up in bed. Sam was tired, having been searching for clues on the demon and Dean was tired too, but someone has got to get it together.

“We will, won’t we?” It was a murmur because Sammy was already drifting off.

“Watch out for Sam” is what his Dad used to say and he never stopped since. Sam might think that he did when Sam went away and broke his heart, but what Sam didn’t know was, that Dean always chose cases in California when one comes up. He’ll swing by, watch him from afar. Watch out for Sam. That’s what he’s going to do. Forever. 


	3. #3

They share the same bed most of the time. Not because the motels ran out of twin bedrooms, but because Sam was crippled by nightmares. 

“For your own safety.” Dean would say to Sam and Sam nodded, although they both know that it wasn’t the the only reason.

Dean ain’t wrong about the safety aspects of their shared bed. Sam would trash around in his sleep and Dean needed to pin him down, keeping Sam from hurting himself or Dean and try to not fall out of the bed at the same time. 

“Shhh..it’s ok, buddy. Sam. Sammy, it’s ok.” Dean would hold Sam tight to his chest, stroking his head and drape his leg over Sam’s body, just to keep him still while Dean hummed a sweet melody.

Dean got this.


	4. #4

Sam woke up with a startle, his limbs started to trash around uncontrollably but it was different to the other nights. There was no Dean in his bed. No strong arms that would wrap themselves around him and calm him down, no leg that would pin him on the bed and hold him in place. 

He sat up, turning on the light and the ugly bright light on the motel’s alarm said that it was almost 2am. 

Where was Dean?

Sam called out for him but Dean was not in their room. He tried calling him on his cell but it went straight to voicemail.

He got up from the bed and paced around the room. Dean’s things were still here, which means that he probably just went out for fresh air. Hopefully. Sam pulled the curtain aside and saw that the Impala was gone.

He told himself not to panic. Told himself to take a couple of deep breaths but it did nothing good to calm him down. 

Dean’s not here and Sam wished that he was.


	5. #5

Sam woke up the next morning. His eyes were red rimmed and they were glued together from the residues of his tears. He remembered crying himself to sleep because Dean was gone. 

_Dean!_

Sam jolted up into a sitting position and before he could start to panic again, he saw and felt Dean stirring next to him. 

 _Thank_ _god_.

“Sammy, let a man sleep, will ya?” Dean’s voice was hoarse and dry.

Sam could shout, could scream, could smack Dean over the head but he didn’t do any of it. Instead, he laid himself back down, snuggled himself close to his brother. Dean’s here, that was all that matters. Sam’s going to give him hell, that’s a given, but not right now. Right now, he wants to enjoy Dean’s warmth, even though he reeks like he had been drinking up the whole bar. Maybe Dean did. Maybe it was Sam’s fault. Was it his fault?


	6. #6

“Time to go out there and look for clues. Find Dad.” Dean had said and Sam knew that Dean was right.

They finish up case after case and Sam was surprised that they didn’t get themselves killed yet but at that rate, he thinks that it’s only a matter of time.

Dean even let Sam choose the music in the car most of the time, that’s the only thing he could give him right now. He wanted to give Sam the world but he couldn’t.

He’s been out drinking more and more lately. Not because he wanted to, but it was more because of Sam. Dean would lie awake, trying to think about a way he could keep Sam safe but he would always come up empty handed.

Well, that was not entirely true, there was a solution. That would be, when Sam would go back to Stanford, go back to his life, get away from hunting. Dean was sure that he could find Dad on his own. He’s no greenhorn and he’s a fairly good hunter. But Dean didn’t want that. Didn’t want Sam to leave him again, so he kept leaving Sam in the night to drink, drown his sorrow in alcohol and he hoped that Sam wouldn’t notice because by dawn, he would always find a way back to the bed Sam was laying in.


	7. #7

“Thank you, sweetheart.” Dean tried his charm on the waitress who just poured him his coffee. “When do you get off?” It was said with a wink and it made Sam roll his eyes to the back of his head.

“Whenever you want me to, baby.” She replied with a smirk and that’s when Sam lost it.

He slammed Dad’s journal onto the table, a little harder than he anticipated, making the coffee spill out of the little mugs and the waitress flinched at his outburst.

“Oh, I’m.. I- I’m sorry.” Sam apologized, blushing and he could see Dean frowning at him.

“No problem, honey, I’ll clean it up.” She walked away hastily, apparently murmuring something about getting a cloth but Sam doesn’t think that she’ll return.

“What was that all about?” Dean asked when he paid and they were sitting in the car.

“Nothing.” Sam replied, biting his tongue because he didn’t want to say that it irked him that Dean flirted so openly in front of him.


	8. #8

Sam heard the Impala roaring into park. He woke up from his nightmare and Dean was gone again. Sam was sure that he met up with that dumb waitress.

Dean didn’t know that Sam was awake when he stumbled through the door at dawn. He brushed his teeth as good he could and chugged off his clothes before he climbed into bed with Sam. Dean automatically pulled Sam into an embrace, big spooning him, as he inhaled the scent of Sam. It wasn’t long before he drifts off to sleep.

And Sam was right when he smelled a women’s perfume on Dean as Dean pulled him close to his chest. There was another scent lingering in the air and Sam knew that scent. It smelled like sex and it made his head spin and his cock hard.

Sam wished it wouldn’t be so complicated, wished that Dean wouldn’t go out looking for sex, wished that Dean would stay with him forever.


	9. #9

Dean hurt himself on the last hunt. He angered a ghost and is now sitting here with a gaping gash across his stomach.

“Hold still, Dean.” Sammy’s trying to patch him up, although his hands were shaking and he might pass out from worry.

“I try to, Sammy.” Dean took another sip of the Whiskey, straight from the bottle. “That son of a bitch got me good, huh?”

Sam didn’t want to say that it wasn’t actually the ghost that hurt Dean. Dean was just clumsy and walked right into that spike of the broken mirror. He didn’t want to be a wise ass - for once.

Dean noticed that Sam’s hands were shaking as he began to stick the needle into Dean’s flesh and he put his hand on Sam’s. “Hey, Sammy. It’s ok. I’m alright.” Dean said soothingly, trying to believe it himself because only then, Sam would believe him too.


	10. #10

They still didn’t find dad. Still didn’t find the demon. Still chasing after nothing.

But Sam still thinks that it was a good day. They bought lunch, it was a warm day out and Dean drove up to the lake. They sit on the hood of the Impala, looking out to the lake and after the meal, Sam laid his head in Dean’s lap as he had his back against the windshield.

Dean twirled Sam’s locks between his fingers, playing with his hair and stroking him over the head. Sam enjoyed it very much. They didn’t speak, didn’t need to speak to understand each other.

“Your hair has gotten long.” Dean said as the threaded his fingers through them.

“I know. I should cut it.” Sam replied, opening his eyes to look up at Dean.

“No, I like them like that.” Dean smiled down and Sam felt his heart flutter strangely.


	11. #11

It was their first fight and Dean didn’t even know what it was all about. Sam’s been ignoring him since he told him at the Diner that he’s coming back later because he had a date with the waitress.

“Oh..” Sam said and Dean could swear that Sam frowned but he couldn’t look closer because the girl was already on him, kissing him hungrily and all Dean could do was throwing Sam the key to the Impala as the girl dragged him along to her car.

Sam was still up when he came home and when Dean asked what was up, he didn’t say a word. Only when Dean didn’t stop asking and pestering him, did Sam unleashed the beast in him.

“Dad’s still missing, Dean!” Sam stood up from the chair abruptly, kicking it back with force. “Do you think fucking a waitress will help us find him sooner?”

Dean stared at Sam, his mouth agape. This side of Sammy, he’d only seen between Sam and Dad but never with him.

Dean didn’t want to argue. Was too lost for words because they would all come out wrong and he didn’t want to make it worse. “I’m sleeping in the car. Let me know when your period’s over.”

He slammed the door close with force and then he stood there, breathing in the cool night air and wondered to himself what went wrong.


	12. #12

“Dean, why do you always have to go out at night? I mean, you can drink in the room too, you know?” Sam’s heart was beating when he asked Dean that question.

Sam had been thinking about phrasing it, went over it in his head so many times and still, it might have come out all wrong and he wished he could take it back. Especially because Dean was looking at him, all confused and since when did his brother get so pretty. Damnit.

“I don’t know, Sammy. Does it bother you?” Dean took a sip of his beer. Sammy was actually right. They drank a lot lately, together. But Dean still needed his space, he goes out, looking for quick fucks because he can’t have what he wants when he stays in the room or could he?

“To tell you the truth, yes.” Sam took a sip of his beer to hide his blushing.

“Why, what’s bothering you?”

“I don’t know. That I’m alone, maybe?” Sam looked Dean in the eye, finding Dean staring back at him, his pupils blown and Sam swallowed hard. “Or maybe that, I don’t know. Whatever it is you’re looking for.. I.. maybe.. I’m..I can give it to you so you don’t have to go out and leave me, again.”

“I don’t know if you can give me what I want, Sammy.” Dean chuckled nervously and when he stood up, he made sure that he turned around quickly, not wanting Sammy to see his boner. “I’ll be back in a couple of hours. Don’t wait up.”


	13. #13

“Sammy, you still up?” Dean was back by dawn, snuggling himself to Sam’s back as he held Sam in his arms.

Sam didn’t say anything. He was speechless as he felt Dean’s body flush against his back.

“Wished you were still up, Sammy. Thought about what you said the other day. Wanted to tell you that I don’t want to leave you at night but I have to. I love you too much. Please don’t hate me.” Dean murmured those words into the nape of Sam’s neck, making the hair on Sam’s body stand up in all directions.

Sam waited a little, trying to put his feelings into words, finding the right ones was the hardest part. And when Sam found the courage to talk back, to actually turn himself around in Dean’s grip, he found Dean snoring next to him.


	14. #14

Dean could hear Sam showering. He wondered if Sam had heard him two nights ago. If yes, he didn’t say anything so Dean thought that maybe it was all just a dream.

Dean turned himself around in the bed one more time, pulling the covers to his chin and refused to get up and face the day but when Sam walked out of the bathroom door, he was awake and his cock was straining painfully against the fabric of his underwear.

“Sammy, you’re not alone in here.” Dean tried to make himself sound annoying, trying to sound like if it was bothering him that Sam walked out of the bathroom naked.

“Why, Dean? Are you afraid of my dick?” Sam chuckled lowly.

“Shut up.” Dean said, blushing and pulling the covers higher up, covering his face and his raging boner.


	15. #15

Dean didn’t imagine his first kiss with Sam to be like this. If anything, he imagined that it would happen in the Impala or within the walls of their motel room. Or even when they are stargazing at night or some other cheesy shit. He didn’t imagine it would be in the dirty and dark alley of the bar where the waitress he had an eye on dared him to kiss Sammy, if he wanted to get it on with her. Dean had never been one who refused a challenge. He’s always in and aiming for the win.

“He’s my brother, sweetheart.” Dean said, looking to Sam.

“Do I look like I care?” She replied, a wicked grin on her face.

Sam nodded his agreement. Maybe he wanted to really help his brother getting laid? They decided to go outside and now he’s here with his back against the wall and Sammy’s chipped lips pressed to his.

It was all sloppy and weird but it was dirty and filthy at the same time and when Sam groaned into the kiss, the waitress was gone. All of a sudden, it was just the two of them. It had never been anyone else anyway, it had always been Sam and Dean.


	16. #16

“Come in, Dean!” Sam yelled to Dean when Sam was waist deep in the water. They finished a case and stopped to grab something to eat. The place was filthy as hell and Sam suggested that they take the food and drive up to the nearby lake. And Dean could never say no to Sam. He never could.

That’s why Dean found himself stripping off his clothes and carefully waded into the water, shuddering as the cold liquid hit his ankles.

Sam splashed water into Dean’s face when he walked deeper towards him, making Dean do the same. Both of them were carefree, like they used to be, when the strain of hunting didn’t eat them up alive.

Sam was so close now, invading his space but for the first time, Dean didn’t mind and the second kiss? That was much better than the first.


	17. #17

Dean still kept going out in the night. Sam’s been awake for almost two hours but Dean was still gone. How could he? After what they had? What they shared? 

Dean never talked about the kiss by the lake. They never talked about it but Sam likes to think back and he gets all tingly when he does think about how his brother’s lips felt so right on his. How Dean’s tongue was so soft against his as they slow danced in his mouth. 

Sam was hard. Thinking about the kiss always made him hard and he would end up rubbing himself off, every time. Today’s not going to be any different.


	18. #18

“Hold still, Dean!” Sam said with a scissor in his hands. “I swear, I’ll cut off your ear if you don’t hold still!”

It was hard holding still. It was hard holding his breath when Sam is breathing so fucking close to his ears that Dean could literally smell what he had for breakfast, could even taste it. The scent of him filling his nostrils and Dean smelled home. Had it always been this way?

“I’m trying, Sammy.” Dean said through gritted teeth, trying to hold in his breathing as not to shake and fall apart when Sam was cutting his hair.

“Almost done.” Sam stood back up, admiring his handy work. “You’re all set.” Sam grinned at Dean and place a peck on his lips as he leaned down a little.

“Now, it’s my turn.” Sam said teasingly but he knows that Dean won’t allow that. Dean doesn’t want him to cut his hair. More to hold on to. He’d say and Sam thinks that Dean’s not wrong.


	19. #19

**Implied Smut.**

It was all about the girls but it really wasn’t.

Dean sent Sam back to their room while he talked to the owner of the Inn.  _“Wanna see if she knows something, Sammy.”_  But Sam knew that it wasn’t about the things she might or might not have seen.

Sam sat at his laptop when Dean walked through the door, his lips swollen and red and that’s when Sam knew that it wasn’t about the girls per se. It was about how Dean still likes pussy and but also, that Dean loves to rile him up.

“Sammy.” Dean smiled brightly, still drunk on orgasm when he walks to the bed and flops down on it. 

Sam couldn’t help but follow, laying on his side next to Dean and Sam could smell the scent of cum filling his nostrils. “You fucked her?” Sam bit his lips as soon as the word left his mouth. He didn’t want to be jealous - except that he was.

“Nah,” Dean breathed out, his hand grabbed the back of Sam’s head and pulled him down, kissing him messily, the taste of the girl still heavy on Dean’s tongue. “she blew me, Sammy. Didn’t even have to ask. She was down on her knees faster than I could open my mouth to protest.” Dean said, as he broke the kiss, forehead still rest on Sam’s. “Does it bother you?” Dean’s finger softly caressing Sam’s cheek. “That I still like pussy?” Sam didn’t answer, instead he pushed Dean into the bed, his tongue invading Dean’s mouth, licking up and sucking in the taste of girl that still lingered. It didn’t bother Sam. Sam knew that Dean’s not going to change his ways - as long as Dean comes back to him. Because that was all that matters.


	20. #20

_Fireworks._

_Sam remembers fireworks._

_It was the best day of his life when he stood out there in the open, peeking up to the sky and watch them go off._

_“I’ve got some for you.” Dean was next to him all of a sudden, with two fireworks in his hand. “Wanna shoot them up?”_

_Of course Sam wanted to and he thought why Dean asked such a dumb question._

Sam thinks back to that a lot. Even now, when they were sitting on the hood of the Impala in the open, backs leaning against the windshield and a beer in their hands. “Wanna shoot them up?” Dean asked, grinning, holding two rockets in his hand. 

“Of course!” Sam smiled back, thinking why Dean could never stop asking stupid questions. 


	21. #21

“I think she likes you.” Dean whispered to Sam when they walked out of the library and the librarian sent Sam a smile, accompanied with a wink.

“She doesn’t.” Sam brushed Dean’s comment off, rolling his eyes to the back of his head.

“Sammy, she looks like she wants to mount you.” Dean teased, ramming his elbow into the side of Sam’s stomach.

“Just stop.” Sam hissed as they rounded the corner to the Impala and when Sam wanted to open up the passenger door, Dean shoved him against the car, pressing his body close to Sam’s.

“But you don’t want her, do you?” Dean whispered roughly into Sam’s ear. “You only want me.” Sam could feel Dean’s crotch hardening in his pants and he couldn’t help but grin. “Only want your brother’s cock because it’s the only thing that can get you off, isn’t it, baby boy?”

“Fuck.” Sam muttered through gritted teeth. Damn Dean. Damn him and his stupid, perfect, dirty mouth and fuck, he’d be lying if it doesn’t turn him on. He loves making Dean jealous and god, jealous Dean is irresistible.


	22. #22

“Man, I look like someone from the Blues Brothers!” Dean groaned as they got their new cheap suits, which was Sam’s idea. **  
**

“No, you don’t. You look more like a.. seventh grader at their first dance.” Sam grinned, as they walked to the car.

“Well, joke’s on you, Sammy. I got laid in seventh grade.” Dean winks and Sam threw him a bitch face.

“Maybe you’ll get lucky today, too, baby boy.” Dean flashed Sam his teeth in a grin.

Maybe he will, Sam thought smiling to himself.


	23. #23

“Hold still, alright?” Sam poked a needle into Dean’s thigh as he tires to stitch up the leg wound.

“I am holding still, Sammy.” Dean clenched his fists, trying to think about anything else but the pain, biting down on his bottom lips as Sam sewed his thigh together again.

“Fuck.” Dean muttered as he exhales and that’s when he realized that he was holding his breath the whole time.

Dean searched for a way to relax himself and that was when he started to humm to himself.

“Dude, are you humming Metallica?” Sam asked, looking up to Dean.

“Yeah, it calms me down.” Dean answered, sweat beading on his forehead.

“You’re weird.” Sam grinned and ducked down again to finish his work.

“Bitch.”


	24. #24

Sam woke up with Dean face buried between his legs and Dean ate him up like he’s a fucking breakfast. **  
**

“Dean..” Dean’s name rolled of Sam’s tongue and Sam couldn’t help but part his legs for Dean, giving him better access. “..what -”

Sam wanted to ask more but he couldn’t, because Dean was coming up from between his legs, attacking his mouth and kissed him fiercely, letting him taste the cum that was still dripping out of his hole from Dean’s fucking last night.

Sam closed his eyes, letting Dean kiss him like his life depends on it. Maybe it did. Maybe they were depending on each other to survive.


	25. #25

“Sorry, man.” Dean said and he meant it. **  
**

“About what?” Sam turns to face him as they sat in the car, ready to drive off from a closed case. They beat a shapeshifter and it was nasty; it brought up the past, things they both wished to be buried deep down.

“I really wish, things could be different, you know? I wish you could just be.. Joe College.”

“Nah, it’s ok. You know, the truth is, even at Stanford, deep down, I never really fit in.” Sam said and he really meant it too.

“Well, that’s ‘cause you’re a freak.” Dean flashed him a wink, accompanied by a grin.

“Yeah, thanks.” Sam couldn’t help but chuckle lightly.

“Well, I’m a freak too. I’m right there with you..All the way.” Dean roared up the Impala, ready to drive off.

“Yeah, I know you are.” Sam laughed now.

“Bitch.”

“Jerk.”


End file.
